


Careful What You Wish For

by thewinchesterlifestyle



Category: Supernatural
Genre: Age Difference, Alternate Universe, Alternate Universe - Slavery, Angst and Porn, Barebacking, Begging, Blindfolds, Bottom Dean, Butt Plugs, Caning, Chains, Class Differences, Class System, Cock Cages, Cock Warming, Collared Dean Winchester, Collars, Cruel Lucifer, Dean Makes Mistakes, Deception, Dehumanization, Dildos, Establishing Hierarchy, Exhibitionism, Extremely Dubious Consent, Face-Fucking, Fingering, Household Hierarchy, M/M, Master Castiel, Master/Slave, Multi, Objectification, Older Castiel, Older Sibling Lucifer, Oral Sex, Orgasm Delay/Denial, Owner Castiel, POV Alternating, POV Multiple, Pining, Power Dynamics, Power Imbalance, Praise Kink, Punishment, Pushing limits, Restraints, Rich Castiel, Rivalry, Rough Sex, Sensory Deprivation, Sex Slave Dean, Sex Slave OMC, Sex Slave training, Sexual Rewards, Sexual Slavery, Size Kink, Slave Trainer Lucifer, Slavery, Sounding, Spanking, Teen Dean, Threesome - M/M/M, Top Castiel, Top Lucifer, Training, Unreliable Narrator, Voyeur Castiel, Voyeurism, establishing dominance, loss of power, maid dean, mentioned past underage, that is basically the tag that explains this, unfair punishment, wealthy castiel
Language: English
Status: Completed
Published: 2018-05-26
Updated: 2018-05-26
Packaged: 2019-05-14 05:03:31
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 7
Words: 12,754
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14763104
Author URL: https://archiveofourown.org/users/thewinchesterlifestyle/pseuds/thewinchesterlifestyle
Summary: Dean has often found himself wishing that he belonged to Mr. Novak instead of merely being the maid the wealthy man employed. Gambling with his freedom as a lower class citizen Dean offers himself up to his employer and Mr. Novak claims him as his newest sex slave. Unfortunately the saying, be careful what you wish for, rings true.





	1. Chapter 1

**Author's Note:**

> Read the tags before continuing.
> 
>  
> 
> This was written for a bunch of connected prompts within the same verse. Each chapter is going to represent a separate prompt but I've decided to post them all in one work instead of making it a series.

Castiel pressed Daniel against the wall, biting down on his slave’s neck near his collar, before he tugged his naked slave into the sitting room. Out of the corner of his eye Castiel could see his maid had just started cleaning the room. He discarded the fact that there was another person in the room and focused on his own pleasure all the while ignoring Dean. It wasn’t like this was the first time Dean had been in the room while Castiel had sought release inside Daniel and it likely wouldn’t be the last.

Dean was his employee and he would either do his job regardless of Castiel’s activities or Castiel would seek a new maid.

“Free my cock and then I want you bent over the couch.” His voice was rough with arousal and his cheeks flushed. It had been a long day and he’d thought of nothing but getting home and fucking Daniel until his stress was gone.

That was the whole point of having a sex slave: a warm body to seek release in whenever he wanted.

Confident fingers went to Castiel’s pants and a warm hand reached inside to free Castiel’s aching cock before Daniel took a step back. He watched the lean lines of his sex slave, how Daniel’s beautiful body moved with each shift of his gorgeous body, before his slave went to the couch and bent himself over.

A perfect round, plump ass was presented to him and Castiel groaned at the sight. Daniel had clearly been born to be a sex slave and Castiel was thankful the sex slave house had acquired Daniel early enough that his training was second nature. When training started later the obedience and service they provided their masters was never as effortless as a sex slave who knew no other life.

His slave was so delightfully obedient, responsive and perfect in all the ways he could hope for.

Idly he could see Dean freezing out of the corner of his eye and casting one casual look over at his hired help he dismissed the young, pretty maid and instead focused on the one waiting to be fucked. There was a reason he’d chosen Daniel, of all the slaves up for auction. Castiel didn’t need to get distracted by a lower class maid no matter how pretty and tempting Dean was when he was bent over cleaning.

His lips curved and he slowly prowled forward until he was right behind Daniel. Castiel’s fingers traced over Daniel’s back and went down to his slave’s ass, parting the perfectly round cheeks to see the large glass plug Daniel _always_ wore for him, before he was tugging it free. “Did you make sure you would be ready for my afternoon fuck?” he asked, hands stilling, as he waited for Daniel’s response. Castiel always made sure to check that his slave had been good, obedient, even when he wasn’t around to enforce his rules.

“Yes, Master. I used extra lube to save you the trouble.” Daniel kept his head down and his hands gripped the couch cushions as he waited to be used. The sex slave house that had placed Daniel up for auction had been very thorough in their training and Castiel constantly found himself pleased at how Daniel excelled at meeting his requirements. Often times Daniel knew exactly what he needed without Castiel needing to say a word.

“Good boy.” Castiel set the plug aside and guided himself inside wet heat. His eyes slid closed as his cock sank into Daniel, spreading his slave’s ass, as he enjoyed the flex of Daniel’s inner muscles around the hard flesh of his cock. “Have you been thinking about me fucking you? My cock pumping inside your tight ass?”

“Yes.” Daniel tried to raise his hips up more and clenched around Castiel’s cock when his master started to thrust inside him. He relished the feeling of balls slapping against him, the way Mr. Novak’s breathing changed and the filthy words his usually well put together master spoke in between thrusts.

When he looked up he could see the maid glancing over at them, a slight flush to freckled cheeks, but Daniel ignored him. He focused instead on his master’s pleasure and the slap of skin against skin. It was his place to provide his master nothing but pleasure and getting distracted by a no-name, lower class servant _wasn’t_ putting his master’s needs first.

Since the first moment during training that he’d received his first cock Daniel had enjoyed being full and used. He was _good_ at being a sex slave, at being a living and breathing toy, and he would continue to do that as long as he was able.

“You’re such a little whore for my cock.” Castiel growled the words and dug his fingers into the flesh of Daniel’s hips. “I bet you love being fucked full of my come. Love knowing it’s locked up inside you when I shove your plug back in.” Castiel pressed Daniel down harder and now he was rutting harshly up against Daniel’s ass, one hand gripping the back of his slave’s collar, while more of his rough words escaped. “You have such a greedy hole. I bet you’d spend the whole day taking cock if you could. It wouldn’t matter which end: either in that pretty mouth of yours or fucking into your plump ass.”

Daniel nodded jerkily. He could feel each time his master’s cock brushed his prostate and the occasional whimper escaped him. His cock, almost always locked away in his cockcage, rubbed against the couch with each snap of his master’s hips. “Please. Master _ohhhh_.” He moaned when a particularly deep fuck nailed his prostate.

The sound had Castiel grinning.

Neither noticed Dean watching them fucking, they were too lost in the heat and friction, as he paused in his cleaning to take in his employer pounding into his slave. He twitched and turned his back to them when the sounds became more frantic.

Castiel’s rhythm was getting wilder, a signal to Daniel how close his master was to release, as the pleasure built inside Castiel and he finally let himself go. His hips jerked in short little thrusts as his cock emptied his load inside Daniel’s ass. Full lips dropped open, parting with pleasure, as Castiel’s eyes slid closed and he allowed himself to focus on the tightness around him.

“Good boy.” Castiel stroked a hand down Daniel’s side, felt the flex of his slave’s muscles around him again, before he eased himself out and reached for the plug. He pressed it back inside Daniel’s hole, watched how it popped inside, before he was stepping away. “I want you kneeling in front of me.”

Castiel seemed uncaring that his now soft cock was still out of his pants as he picked up the paper from the table and settled himself in his chair. He watched Daniel remove himself from the arm of the couch where he’d been bent over and walk over to drop gracefully to his knees before Castiel on his pillow.

Blue eyes flicked to the cockcage his slave wore, pleasure at the sight had him smiling, as Daniel waited for his next instructions.

“Clean my cock.” He spoke softly as Daniel braced himself before leaning forward to take Castiel’s cock into his mouth. Warm heat around the sensitive flesh had Castiel’s breathing stuttering but he calmed himself and enjoyed the sensation of a warm mouth cleaning the mess from him.

His fingers stroked through Daniel’s dark hair and when his slave went to lean back after finishing he stopped him with a soft sound.

“I want you putting that mouth of yours to use.” Castiel watched as Dean moved to clean the right side of the room, “Keep my cock warm and later I might let you come when I’m fucking you into the mattress.” He didn’t bother to hide the smirk that crossed his face when he saw Daniel’s eyes widen at the thought of getting release. “But I expect you on your best behavior. No interrupting me.”

Daniel didn’t say anything and instead shifted himself as he made sure to keep Castiel’s soft cock resting in his mouth. He allowed his eyes to slide closed and focused on breathing through his nose when those long fingers returned to petting him as Castiel read the paper.

He could barely hear the maid moving around, cleaning and ignoring the scene, as he focused on obeying his master’s orders and silently hoping that Mr. Novak would let him come when he was getting fucked later in the evening. The sounds of movement off to the side soon faded when Dean left the room to move on to another and Mr. Novak sighed as he continued to pet Daniel’s head while relaxing after his much needed fuck.


	2. Chapter 2

**Notes for the Chapter:**

> Now the 'sex slave Dean' tag starts coming into play.

Mr. Novak’s sex slave wore a cockcage and a collar at all times. There were times he wore revealing clothing and other times he went completely nude. Neither option was unusual for a sex slave in their society. There was always a glass plug showing between his cheeks for easy access and Dean had lost track of the number of times he’d seen the sex slave on his knees before Mr. Novak with Dean’s employer’s cock resting in his mouth.

Like all sex slave owners Mr. Novak made good and thorough use of his slave.

Dean heard the moans, the sounds of Mr. Novak’s bed hitting the wall and various noises that all signaled the same thing: Mr. Novak fucking his sex slave. There were several times he’d stumbled across Mr. Novak burying himself in the slave and other times he would be ordered to keep cleaning while Mr. Novak used his slave in the same room in a number of ways that had Dean flushing with arousal.

Those were the times Dean could hear every filthy thing that passed Mr. Novak lips and others he could only hear muffled words. He could see the way his handsome employer manhandled his slave, how he twisted his fingers inside the slave’s hole, before he was pressing an impressive cock inside and fucking with a driving force that had Dean’s cock hardening.

It was why, every time Dean had watched as he cleaned, he would go out and let the first interested man fuck him. It didn’t matter if it was in some back alley, in the grass or some cheaply rented room. Dean _needed_ to imagine it was Mr. Novak holding him down, roughly taking him and leaving him with an ache that burned with each step he took when the nameless man finished fucking Dean wherever they had ended up.

Unfortunately that wasn’t the same and years of frustration, he’d started cleaning Mr. Novak’s at an early age and now he was in his prime, and seeking release with others Dean made an impulsive decision without a thought to the consequences.

Dean started wearing tighter clothing and smaller uniforms to get Mr. Novak’s attention. He had never thought he would be jealous of a sex slave, one of the lowest classes in their system and even lower than him, but he wanted to be the one Mr. Novak was pounding into. He wanted to be the one split open on that impressive cock but that wasn’t his class. It didn’t mean he was going to give up trying for at least one good fuck from the wealthy man.

Filthy, low class men eager for rough and dirty fucks wasn’t what he wanted even if it was all he had each and every night he left Mr. Novak’s home.

Dean’s clothing got progressively scarcer the more he heard or came across the sex slave getting fucked and then spent a night moaning under the wrong man. It came to a head one day when Dean knew Mr. Novak would be coming home and he laid himself out on the table right in the entry way.

It was desperate, thoughtless and stupid but it didn’t stop him from doing it.

He had discarded his clothing, worked a plug inside his ass so he was open, before presenting himself on the table. It was his only chance and he felt his breathing shutter when the door opened. Dean could hear the slave coming into the room for the typical afternoon fuck that Mr. Novak  _always_  enjoyed only to freeze at the sight of Dean laid out.

Dean watched grey eyes narrow on that handsome olive toned face as the sex slave looked him over and then glanced at his master to see the pure lust filling Mr. Novak’s bright eyes. “Master?” the slave’s voice rung out in the empty entryway as Mr. Novak took his coat off to hang up, toed his shoes off and closed the distance between Dean and himself.

By putting himself in the position he had Dean knew of the potential outcome. He could lose his place in his current class but he’d been thinking about this for several years and there were worse things if it came down to it. Fingers touched him before Dean was pulled forward for Mr. Novak to bite down on Dean’s neck.

Dean whimpered at the feeling as his naked body was dragged close and he could feel Mr. Novak’s hard cock through his pants.

“Been thinking about fucking you ever since I saw you.” He turned Dean around and stared at the plug he could see between Dean’s cheeks. “Ready for me?” the voice was rough as Mr. Novak tugged on it. “I’m going to wreck your ass.” It was a promise as he tugged the plug out, placing it aside, before freeing himself. Wordlessly he bent Dean over the table so his green eyed maid’s ass was presented and Dean’s hands were on the table.

It was only seconds before Dean felt the blunt head of Mr. Novak’s cock and then it was pressing inside him, stretching him open, as Mr. Novak worked to bury himself all the way in. Dean had clearly not prepared himself enough and the burn had his mouth falling open on a hitching moan.

“So fucking  _tight_.” Mr. Novak gritted as his fingers dug into the flesh of Dean’s hips, “You were born in the wrong class. Body made for sex. Made to take cock.” Dean whimpered as Mr. Novak finally bottomed out balls deep inside him.

Dean could feel the sex slave’s eyes on him, he could feel the envy burning into him from narrowed grey eyes, as Mr. Novak drew back and snapped his hips forward to slam back in. The feeling had a moan escaping and Dean shook as Mr. Novak went right into it. There was no easy thrusting, letting Dean get used to the feeling of being full of cock, it just went straight to a fast and brutal pace that was jarring his whole body.

It was _very_ familiar to the rough, emotionless fucks he experienced every night but the difference was that it was Mr. Novak inside of him. The man’s hands were soft, his skin smelled clean and fresh, instead of the filthy and foul smelling men who pawed at him before shoving in without an ounce of care.

Every few strokes Mr. Novak’s cock managed to brush the bundle of nerves inside him and sent pleasure dancing across his nerves as he gasped, ass clenching and pushing back, while Mr. Novak spoke.

“Greedy for cock.” Mr. Novak’s voice was rough and Dean nodded rapidly, “I’ve been imaging owning you. Bedding you whenever I wanted and chaining you to my bed. I’ve thought of shoving you down to your knees and fucking your mouth, bending you over and pounding into your hole until you can’t sit down.” His fingers gripped Dean’s hips to pull him back into his thrusts. “I can’t wait to tie you down and use you until you’re hoarse from screaming.”

Dean tried to grip something but he couldn’t get a good grasp as Mr. Novak picked up his pace. There was pure greed in the movements, a man of high class chasing his pleasure in a warm body he felt entitled to, as the slap of skin against skin echoed in the entryway.

The pleasure that built was hot, something wild, as Dean reached to grab himself but Mr. Novak gripped his wrists to hold them down. “ **No**.” it was growled, “Your pleasure is  _mine_ now.” The tone was possessive. “ _You’re_   _mine now_. _Only I decide if you find release or not._ ”

Dean pressed his cheek against the cool wood and shifted his legs as Mr. Novak pounded into him. He could hear the moans and growls escaping the higher class man.

At some point he registered the slave leaving the room but he didn’t think about where he might be going. He didn’t care when the other guy returned and waited silently as his master fucked Dean over the table.

“You’re so good at taking my cock.” Castiel snarled as he neared his orgasm before reaching around to grip Dean’s cock. He teased the head of Dean’s cock and felt the younger man trying to thrust into his hand. A _boy_ , really, if Castiel was being honest. Dean was a foolish lower class _boy_ who clearly hadn’t thought of the consequences of offering himself in such a way to someone of Castiel’s station. Barely eighteen if his employment papers had been truthful.

Despite that Castiel was hardly going to pass up the opportunity this presented. Two sex slaves were, after all, better than one.

The combination of Mr. Novak fucking him and gripping his cock set Dean off as he wailed his orgasm, cock spilling onto the floor and Mr. Novak’s hand, but the man kept thrusting until his cock was jerking and spilling inside Dean.

“My new slave.” The words hung in the air as Mr. Novak gripped Dean’s body. They were possessive and Dean could feel them like a weight settling around him. The consequences of his actions were completely obvious and Dean could not turn back now that he’d gotten what he had wanted.

Castiel stayed there, pressing Dean down, before easing back as his cock slipped free. He simply held his hand out as his slave placed a plug into his hand so he could work it inside Dean before he was hauling him up onto his unsteady legs.

Dean wavered slightly as he watched Mr. Novak taking something from the slave and then he felt something cool settle around his neck before it was locking into place.

A collar.

It was the mark of a slave and Dean knew this particular collar marked him as a sex slave. He ignored the other slave’s gaze and instead focused on the warmth that radiated from Mr. Novak as his new  _master_  took him in.

The blue eyes staring at him were dark and possessive as they moved over his form. Dean shivered at the intensity and that was when Dean noticed the other man in the room. When he noticed Mr. Novak’s older brother staring at him a shiver raced up his spine. “My my Cas. It looks like you got yourself another sex slave and you didn’t have to pay a penny.” He stepped further into the room, “And a pretty one at that.”

Dean flushed as he felt Mr. Novak’s fingers tighten on him before the man was turning to fully regard his brother. “It must be my lucky day,” He tucked himself back in his pants without a hint of modesty before focusing on his brother, “To now have two beautiful sex slaves to service me whenever I should choose.”

While they spoke Dean glanced sideways at the sex slave who was glaring at him silently. He could see the challenge in those grey eyes and gave a matching look back. There was only an ounce of regret about Mr. Novak’s claim and the meaning behind it but the well fucked feeling had him sighing softly in contentment. He hoped he was the one Mr. Novak chose to warm his bed at night.

He wouldn’t be enjoying anymore back alley fucks or rough sex in the cool grass with nameless men.

Once Michael left Mr. Novak turned once more to regard Dean. “You belong to me.” He spoke softly as he tilted Dean’s chin up. “I shall have to hire a new maid and have space made for you. Michael is being kind enough to get the proper paperwork for me to register you as my property and to make sure the records show your new status. It was very fortunate that he witnessed you willingly lowering yourself and giving up your claim of status.” Dean shifted on his feet but kept Mr. Novak’s gaze until he was told to look away. “I will get you your own cockcage and a new plug along with a few other items I expect you to wear when told.”

Dean nodded and earned praise as Mr. Novak began to guide him upstairs. “Master?” the voice came from behind them and Dean felt Mr. Novak freeze.

“Yes Daniel?”

“Is there anything you need me to do?”

“Go to my bedroom and wait for me there on the bed.” He continued guiding Dean up the stairs and towards the bathroom. “I’ll have to use one of Daniel’s cockcages on you until I can purchase some toys to use on you.” He removed the collar around Dean’s neck, set it safely out the way before showing him to the shower. “Once you have cleaned yourself put the collar back on. I will have your official collar made and delivered as soon as possible.” He stepped away, blue eyes moving over Dean’s bare form with appreciation, before stepping out of the bathroom and leaving Dean to start cleaning himself off.


	3. Chapter 3

**Notes for the Chapter:**

> A few months after the previous chapter...

Castiel allowed his eyes to travel over both of his pretty sex slaves. He could see light bruises on Dean’s hips from that morning and bite marks on Daniel’s neck from the night before. The sight of them always filled him with arousal and he had wanted to try enjoying them both at the same time for a while now. It had been half a year since he’d acquired Dean as a second sex slave and it seemed a waste to leave one of them untouched.

It seemed a shame to only use them separately instead of at the same time. Two sex slaves should make things far more interesting and enjoyable in the long run.

Both of them wore cockages with a glass plug in their holes to keep them open and their collars rested snug at their throats. He loved how thoroughly owned they looked and how they contrasted. Daniel with his dark hair, grey eyes and beautiful olive skin and Dean with lighter hair, pretty green eyes and freckled skin had started to lighten now that he wasn’t working outside in the sun. Together they were a pretty picture and Castiel was very sure they would look beautiful moving together.

Besides Daniel really deserved a reward and Castiel was very sure that letting Daniel fuck Dean’s perky ass would be a treat his first sex slave would enjoy.

“Dean. I want you to undress me.” He watched his sex slave comply as Daniel watched them silently, “Then I want you in the center of the bed for Daniel.”

At the sound of his name the other sex slave looked at his master and waited for further instructions.

“Daniel…I want to try something new.” He grinned as Dean worked on his pants, “You’re going to fuck Dean while I’m fucking you.” Castiel didn’t notice the look on Daniel’s face when he allowed Dean to remove his shirt and then Dean was finishing up.

His cock was hard and excitement was racing through him. Castiel counted himself lucky that he had two beautiful and eager sex slaves to service him. Even without the years of training that Daniel had Dean was turning out to be a delightful sex slave and Castiel greatly enjoyed having a choice between the two.

Dean stepped away from him and moved to the bed to comply with his instructions. “Place some pillows under your hips to give them some lift.” Dean did as he was told and tried not to show his reaction to the knowledge that Daniel was going to be fucking him.

The very thought had a knot in his stomach as he glanced over to see Mr. Novak freeing Daniel from his cockcage. The other sex slave’s cock hung free, surprisingly thick and getting noticeably hard, as Mr. Novak instructed Daniel to use the lube to get himself harder.

It was an impressive cock but not the one Dean wanted and he gripped the sheets before lifting his hips up as the bed dipped. “Make sure you fuck him good.” Mr. Novak spoke and Dean blinked at the realization that Mr. Novak was going to watch before fucking Daniel.

His plug was pulled from his ass and he clenched around nothing as Daniel pressed the head of his cock against Dean’s hole. It wasn’t slow or easy as the other sex slave just slammed himself inside with a greedy snarl.

The feeling had Dean wincing, not a single ounce of lube had been added, and biting back a whimper at the sudden stretch as fingers dug into his body. With each hard thrust the bed shifted under them and Dean whined in pain as Mr. Novak climbed onto the bed.

He wasn’t aware of when Mr. Novak had buried himself inside Daniel but he could feel the extra weight and the harsher movements as Mr. Novak fucked Daniel while Daniel was fucking him. It had Dean struggling to grab air and panting when Daniel made his movements harder, intentionally avoiding Dean’s prostate, until fingers knotted in Dean’s hair to yank his head back.

Dean went with the motion as he clenched his eyes and he whined at the pain it was causing.

Castiel was letting Daniel shove himself back onto his cock even as he snapped his hips forward to meet his slave’s. It was a harder and quicker pace he attributed to the fact that Daniel hadn’t been able to fuck anything in a while, the last time had been Michael’s slave Anna and the two slaves had put on a beautiful show, but it was a pained sound from Dean that caught his attention.

“Dean?” he paused in his movements and it was a few more thrusts before Daniel stopped moving. Castiel pulled out of Daniel and instructed his slave to get off Dean. He could see darker marks where Daniel had dug his fingers in and the way Dean’s fingers were clenched in the sheets. “ _Daniel_.” The name snapped out. He hadn’t thought he would have to tell his slave to not be that rough on Dean. “Hands against the wall and legs braced apart.”

He watched Daniel move across the room as he placed his hands against the wall. It was rare that Castiel had to punish either of his slaves, there were a few times but it wasn’t often, and now he collected the paddle before going to his slave.

“I shouldn’t have to tell you not to harm him.” Castiel brought the paddle down hard across Daniel’s ass before he kept swinging it. The sound of skin being struck filled the room, “Dean, I want you to watch so you know the kind of punishment such an action earns.” There was a hiss of pain from Daniel but the slave bit it back as best he could. “I was going to let you come in his ass. You were being rewarded with an orgasm.” He kept hitting as Daniel’s ass turned bright red, burning harshly, until Daniel sobbed out. “I’m disappointed.”

Castiel resolved that next time he would monitor the situation closer and make sure Daniel wasn’t causing too much damage to Dean. After all if Daniel damaged Dean then Castiel would need to take his slave to the doctor and then he’d have to wait for Dean to heal before he could get any use out of his slave’s ass. It would be a waste of money.

Slowly he tied Daniel’s hands behind his back and shoved him down into one of the chairs in his room so he had a good view of the bed. “Now you can see what you are missing out on.”

Daniel watched Mr. Novak sitting Dean up carefully, removing his competition’s cockcage, before laying Dean out on his back. Mr. Novak was typically rougher, he loved to pound into his sex slaves’ asses and get off with grunts and groans, but now he moved carefully.

He watched, silently furious, as Dean’s wrists were being pinned to the bed while Mr. Novak rolled his hips forward at a slower pace. He was rocking up against Dean’s body, cock brushing Dean’s prostate to pull out moans, as Daniel watched with a burning ass while tears slipped down his cheeks.

He  _hated_  Dean in that moment more than when he had watched his master first fuck Dean and claim him as a second sex slave. _Dean_ was supposed to remain the maid. He wasn’t the one who had spent years being rigorously trained as a sex slave, learning how to give pleasure and learning the feeling of being used in a variety of ways so he would be good for his master, not like Daniel had been.

Dean was going to earn his master’s approval again, he would go out of his way to pleasure Mr. Novak, until he was once more the center of his attention. Daniel remained silent as Mr. Novak brought Dean to orgasm with his hand, still fucking forward at a sedate pace, until he was shooting is release inside Dean.

It wasn’t the end.

Mr. Novak continued to tease Dean to hardness and then send him over the edge again and again until Dean had nothing left to give. Long fingers stroked the soft collar around Dean’s throat as Dean panted harshly, body limp and thoroughly fucked out, before he was climbing off the bed.

Blue eyes trained on him and Daniel lowered his eyes to the floor until a warm hand was tilting his chin up, “I’m sorry, Master.” Daniel spoke softly, “I wasn’t thinking. I lost control.” Which was a complete lie but he wasn’t admitting that.

“You are forgiven.” Mr. Novak spoke and locked eyes with Daniel, “I’ve had you for years and I know you’re such a good boy for me. We’ll try again later but if this happens again…” he trailed off and stared at Daniel with hard blue eyes, “I would hate to have to employ harsher punishments to curve such behavior.” Daniel nodded and did his best not to melt at the soft hand that stroked his hair. “I will not be calling for you tonight.” It felt like a punch to the gut since Daniel was _always_ the one who warmed Mr. Novak bed at night, “Show me you can behave and that will change tomorrow. I enjoy you in my bed and I love having you underneath me, moaning like a good little slave. Show me you’ve learned your lesson.”


	4. Chapter 4

**Notes for the Chapter:**

> Another little time jump and Lucifer enters the picture...

Dean lay in his room listening to the sounds of his master’s headboard banging against the wall and Daniel’s loud, pleasure filled moans. Mr. Novak had spent most of the morning, from the sounds of it, teasing Daniel until the other sex slave had been near sobbing.

Now they were on round two and as the headboard hit the wall harder, at an increasing pace, Dean knew Mr. Novak was close to a second orgasm. Usually he was the one getting fucked in the morning, not Daniel.

It had been weeks since Daniel had been punished and Dean had gotten less attention after Daniel’s punishment had ended. Usually Dean was the one that Mr. Novak fucked in the morning and Daniel got preference at night but for the past week Dean had only been occasionally used when his master first got home. The bulk of Mr. Novak’s attention and arousal had been focused on Daniel who was more than happy to rub it in Dean’s face when their master was away.

He shoved his face against his pillow and tried to ignore how loud Daniel was being. Being constantly caged and plugged, aroused by the sights and sounds of his master, was torture when he couldn’t seek release. Abruptly the banging stopped and silence filled the house. A few minutes passed before he got up from the bed and went into his bathroom to get around.

The shower was mercifully hot and he wished Mr. Novak didn’t keep him constantly in chastity but the cockcage Dean almost constantly wore was designed specifically for sex slaves. With Mr. Novak keeping the keys with him there was nothing Dean could do.

Once Mr. Novak left it was mostly a typical day. He wore his collar, his cockcage and the plug even as he moved through the house. Today, the weather a bit colder, Mr. Novak had given him permission to wear the pair of sheer pants that his master let him wear in the winter while he was at work. The material clung to his ass and bending over allowed anyone looking to _see_ the plug spreading his cheeks.

Whenever Dean ran into the other sex slave Daniel made sure he saw the marks their master had left on him, the bruises from fingers gripping his hips and bite marks from Mr. Novak getting rough.

Dean scowled at him when Daniel’s back was turned and did his best to ignore the other sex slave. He hated that Mr. Novak had taken to giving Daniel more attention in an effort to show his first sex slave his status hadn’t changed in the household.

Daniel was still ranked first.

The servants in the house, both bought and hired, moved about cleaning and cooking. It was completely normal until the front door opened to reveal a man Dean had only seen a few times when he’d worked as a maid.

Lucifer Novak.

The man wore a sharp suit and his eyes were equally sharp as they surveyed the house. He stepped further inside and it was only a few minutes before Daniel was greeting him. Dean watched Lucifer regarding the other slave with something of blatant lust.

It had Dean shifting on his feet. “I know how much you enjoy when I come over to use you but I’m afraid I’m interested in trying my little brother’s newest slave out first.” The words had Dean’s eyes widening, “I’ll seek you out after I’m finished giving him a test drive.”

Daniel was nodding and offering that same smile that he gave to their master.

Then Lucifer was staring over at him and Dean could _see_ the malicious smirk Daniel was throwing his way. The look had dread welling up inside of him. Lucifer closed the distance before guiding him out of the main foyer, up the stairs and towards the bedroom. “Which one is yours?” his voice was smooth and low as Dean turned towards his small room. “Thank you, slave.”

The door was opened and Dean felt himself pushed inside by the hand at the small of his back. If he was still a maid he could have said something but a sex slave had no rights and this was his master’s brother. He was to obey Mr. Novak’s family and to respect their position within society.

“I heard from Castiel that there was an issue between his two sex slaves.” Lucifer spoke calmly as he started to strip himself. He carefully draped his clothes over one of the chairs in Dean’s room. “Imagine my surprise when I heard his gorgeous little maid was his newest slave. What a lucky little bastard my brother is to have gained such a pretty little thing.” A smirk tugged at his lips, “Giving up _all_ of your rights was foolish, little slave.”

Dean couldn’t stop a whimper when Lucifer reached to touch him through his soft pants. The tease of fingers against his caged cock had him pressing forward without thought. He was a tactile person by nature and Mr. Novak’s neglect, his inability to seek release elsewhere, was driving him insane.

“He’s been neglecting you in favor of Daniel, hasn’t he?” Lucifer’s voice was lower and Dean blinked at him. “While Daniel is a good fuck, very vocal, he has nothing on your looks. Though that might be my personal preference. I like lighter hair, freckles and generous, cock-sucking lips. If you were mine I wouldn’t let you out of my bed very often.”

“I can’t…Mr. Novak is my—”

“And you’re not going to say anything to my brother about my using either you or Daniel, are you?” Dean could hear the edge in Lucifer’s voice and shook his head. He knew things like this happened in other households and it shouldn’t have come as a shock that any of Mr. Novak’s brothers might borrow his slaves. “Good. Now strip off those useless pants and bend over the bed.”

Dean thought back to the day before when Mr. Novak had bent him over the couch for a quick fuck and the way he’d spent most mornings and nights listening to his master using Daniel.

His hands went to his pants and he pulled them down before moving to comply with Lucifer’s instructions.

Warm hands spread his cheeks apart and he knew Lucifer was inspecting him. The plug was pulled free shortly after and once more Lucifer examined his hole. A few fingers pushed inside him and crooked.

“Such an obedient slave, one not even properly trained, shouldn’t be neglected like Castiel is doing with you.” Lucifer stroked against his prostate and Dean’s hips rocked forward against the mattress. “You need regular use and maintenance. You need a firm hand to train you how to properly behave and please your master. Castiel’s neglect is harming your ability to be the best sex slave you could be. He is taking unnecessary risks not training you into being obedient and eager.”

Dean sighed at having hands mapping his body and touching him, teasing him to the edge, before a cock was pushing into him. His eyes slid closed and his mouth dropped open at the feeling of being full again. It wasn’t Mr. Novak but it was worlds better than all of those dirty fucks he’d used to satisfy himself with before Mr. Novak claimed him.

Lucifer’s cock felt thick and long as it started to pump in and out of him.

It wasn’t long before Dean was moaning and shoving himself back into Lucifer, ass tightening each time Lucifer’s cock hit his prostate. “Castiel doesn’t know what he has, does he?” Lucifer asked while he continued fucking into Dean. “What a waste. He favors Daniel, treats him so much better and what do you get? Neglect, right? You were practically born to be the perfect sex slave, a perfect body and deliciously responsive, but he’d ignoring that fact.”

Dean clenched his eyes shut and tried to push the words from his mind but they were ringing true. Mr. Novak favored Daniel due to his status as his first sex slave. He let Daniel warm his bed at night and used him far more often than Dean after the first few months of Dean being a sex slave had passed.

His master had never offered to let Dean fuck Daniel but after the first time and Daniel’s punishment Mr. Novak had let Daniel fuck Dean three times. Dean had been forced to walk around with Daniel’s come plugged in his ass while the other slave had rubbed it in his face.

Doubt started to grow in Dean’s mind but Lucifer’s touch and the feeling of Lucifer fucking him distracted Dean. He let himself fully participate up until Lucifer came in his ass with a sound of pleasure.

Slowly Lucifer pulled out and pressed his plug back inside. The man didn’t say a word and Dean could hear him cleaning up before dressing. It wasn’t until he reached the door that Dean heard him speak again.

“I’d take much better care of you. That gorgeous ass of yours would be in near constant use and I certainly wouldn’t neglect you for another slave.” Then he was gone.

Lucifer stayed in the house for hours and at one point Dean walked by to see him fucking Daniel on the couch, viciously pounding into the other sex slave, before Dean continued on to the kitchen for something to eat.

When Mr. Novak came home Lucifer was waiting for him in the sitting room, poised and put together once more. “Lucifer.” There was surprise in the tone as Dean stood around the corner listening. “I didn’t know you were stopping by.”

“I wanted to inquire about a purchase, Castiel.”

“Oh? What were you interested in purchasing?” Dean looked around the corner and watched his master pouring his brother a drink before pouring himself one.

“One of your slaves. You mentioned having difficulties between them and I’m very interested in acquiring Dean for myself.” Something like shock went through Dean but he remained in his place listening.

“Dean?” Dean could hear the surprise, “You want to purchase him?”

“Yes. I’m looking for a new sex slave, my last slave had to be put down, and truthfully I had admired him before when he was simply a maid.” The sound of a glass being set down on the table reached his ears. “Are you willing to part with him? I’m willing to pay whatever you feel he’s worth and it would eliminate your problems with Daniel.”

Dean clenched his hands and closed his eyes. He calmed his breathing and tried his hardest not to make a sound. “It’s a possibility.” Mr. Novak finally spoke, “Daniel had never acted up before and was nothing but obedient until I claimed Dean. I’m trying to fix the problem myself but if it doesn’t correct itself I will have to part with Dean. Whether it is through selling him or having him put down.” Dean jerked at Mr. Novak’s words, horror and fear creeping up, as the options for him in his new class were presented.

He knew sex slaves were repeatedly sold to new masters, sold to a whorehouse or put down. There were no other options for someone in the lowest class.

“I’ll buy him from you today and you won’t have to worry about making the choice to terminate him.” Lucifer was leaning forward when Dean glanced around the corner to look at them. “If you find in the future you want to borrow him or simply come over to my home to use him I’d have no problem with that. You will have eliminated your problem and you could still fuck Dean when the need arose. It’s the best of both worlds.”

Mr. Novak was swirling his glass, the liquid sliding against the edges, as he thought about Lucifer’s words. He was opening his mouth when a hand closed around Dean’s wrist and he found himself being yanked away from the doorway.

Daniel glared at him in disapproval and started hauling him away from the sitting room. “I hope you realize the punishment for  _spying_  on our Master.” His tone was disapproving and Dean glared back. “I have no idea why he would have bothered claiming you. You were a _worthless_ maid and you’re an even more _worthless_ sex slave. You didn’t even receive proper training for it.”

“You—” Dean was cut off when a voice sounded from behind them and the two slaves stepped apart quickly. Both of them dropped their eyes to the floor as footsteps came closer until Mr. Novak stopped in front of them.


	5. Chapter 5

**Notes for the Chapter:**

> Now you get to find out some of the outcome of Castiel's talk with Lucifer...

Daniel’s heart was pounding with anticipation. He had  _full permission_  to fuck Dean whenever he wanted while his master was out of the house. Eagerly he assumed his master’s favorite position, ass up and face down, in the center of the bed as his plug was pulled out. He made sure his legs were spread as wide as possible to present his ass and that his back was bowed in absolute submission as Mr. Novak preferred.

A little lube was added to slick his hole and then he was being filled up with his master’s long, thick cock. His mouth dropped open on a gasp when it brushed against his prostate and he instinctively tightened down.

If he had needed any proof he was his master’s favorite this was all it took. Dean had  _never_ gotten permission to fuck him and the power this gave him over the other slave was heady. His cock actually twitched in anticipation because once his master was done fucking him into the mattress for his morning fuck Daniel’s cock would be free from his cockcage for the entire day.

He moaned and gasped, “Master! Ohhh please Master please. Harder!” just as he knew Mr. Novak enjoyed and shoved himself back to take his master’s cock deep each time. Heavy balls slapped against his ass and the headboard knocked against the wall. He had been fucked and used countless times since his training years and years ago but none could top his master.

Daniel  _knew_  Dean could hear them and he let out an even louder, filthy sounding moan. Mr. Novak pounded into him, fingers dug in and grunts of pleasure filled the air. Underneath them the mattress groaned in protest of the rough fucking and Daniel relished the feeling, the sounds and the jealousy he knew Dean was burning with in the room over.

His body burned with arousal, his orgasm held away from him, as Mr. Novak moved faster and rougher until he came with a deeply satisfied moan. Warm, strong hands freely touched his naked body and teased his nipples before retreating.

Slowly the softening cock slipped from his ass, come leaking out after and Daniel clenched up until his plug pressed against his hole. It slipped inside and caught on the furrowed end giving him a nice full feeling.

He lay there as Mr. Novak cleaned up in the bathroom, dressed and turned towards him with the key. “As I explained last night you now have permission to fuck Dean while I’m away. This is as much of a reward as it is a way for you to get used to him being a, hopefully, permanent fixture in my household. Hopefully the closeness will help both of you or at least help you both come to an understanding. If I remember right fucking can be used to establish and maintain a hierarchy. Maybe that’s what is missing?”

Daniel barely held back the sigh of relief when his cock was freed and the cockcage was carefully put away. He waited until Mr. Novak had been gone from the house for an hour, an hour of him working himself up and feeling excitement buzzing under his skin.

Dean was in the sitting room when he found him, wearing a pair of loose fitting pants and the memory of the few times he’d fucked Dean had his cock hardening. The other sex slave was always kept tight, the plug Mr. Novak used just enough that pushing in wouldn’t tear Dean, and Daniel looked forward to that feeling. “Bend over the couch.” His voice was rough when it came out and Dean’s head snapped up to stare at him incredulously.

“Are you serious?” the tone was full of disbelief but Daniel had their master on his side and he had complete permission for this. If Dean didn’t obey him then he would tell their master and Dean would be _punished_. Daniel knew, with that punishment, that Mr. Novak would let him fuck Dean regardless.

“Take your pants off and bend over the couch.  _Now_.” He kept steal in his voice and stepped into the room.

Dean glared at him but slowly climbed to his feet and Daniel could remember the shock on Dean’s face the night before when their master had explained his meeting with Lucifer. He watched as Dean very reluctantly removed his pants, bending over and showing off the plug buried in his ass to Daniel before Mr. Novak had encouraged Daniel to use Dean.

He waited until Dean was bent over the couch and walked over to stand behind him. Daniel admired the view, he could appreciate a plump ass like Dean’s, before he shoved his pants down and stroked his cock to full hardness.

A few groans escaped and he relished the knowledge that he got to be in charge, that he could set the pace and it was going to be his cock buried in a sex slave’s ass for his own pleasure. His hips jerked forward and his eyes hooded as his breathed heavily.

“I hope you’ll be good for me like our Master ordered you to be.” He removed a hand from his cock and tugged on Dean’s plug before pulling it free. Dean gasped and Daniel watched how his hole clenched down on nothing. “I’m going to enjoy fucking you all day and coming in that tight ass of yours so you’re walking around full of _my come_.”

He could hear Dean mutter something against the couch cushions but Daniel didn’t care as he sunk into tight heat. Every single inch he pushed inside had his breathing increasing and his cheeks flushing. Dean’s hole was sinfully tight and just slick enough to ease the way.

This was the very first time he’d gotten to fuck someone else for his own enjoyment without orders or someone else watching. Daniel was going to relish it and when he had bottomed out his eyes closed in bliss.

Dean’s ass was _tight_ ; clearly a sloppy prep on the other slave’s part but Daniel preferred it. He rolled his hips back and snapped them viciously forward with a grunt. Pleasure jolted through him with each snap of his hips as he pumped his cock in and out of Dean’s clenching ass.

His balls slapped against Dean’s ass loudly and Daniel saw little point in holding back how much he was enjoying himself. “ _Fuck_.” The word escaped his lips as he rapidly pistoned his hips forward as he fucked and fucked and _fucked_.

Occasionally he hit Dean’s prostate and it startled a moan out of Dean. The sounds that Dean reluctantly released, he could tell Dean was trying not to moan, had him grinning smugly. “ _Ohhh hhh_ —”

The choked off sound had Daniel’s fingers digging in as he worked himself forward quicker, drawing closer and closer to his orgasm. It twisted inside him, warmed his gut and when it finally crashed through him he had slammed himself balls deep with a groan.

Daniel’s hips jerked forward a bit as he draped over Dean and struggled to calm his pounding heart. Slowly he moved away from Dean and moved back so his softening cock slipped from Dean’s sloppy hole.

He gave himself a few moments to watch his release leaking back out and with a grin pressed his come back inside before inserting Dean’s plug. “I feel less tension already.” There was a curse from Dean as he struggled up and glared at him. “I think our Master was right giving me this reward.”

“Fuck you.” Dean’s eyes were narrowed and Daniel looked at the flush of arousal on Dean’s face from their recent fucking.

“You’re the only one getting fucked.” And the fury that comment earned him only filled him with more smugness. He had every intention of seeking Dean out as often as possible now. Daniel was enjoying the sated, loose-limbed feeling of a good orgasm far too much to hold back.


	6. Chapter 6

**Notes for the Chapter:**

> This chapter is focused on all of Dean's sex slave training. It is the other result of Castiel's conversation with Lucifer...most of the tags are for this chapter.
> 
> The tag 'unreliable narrator' also comes into play here. Keep in mind that just because Lucifer thinks something is the cause/reason/etc behind the problems in Castiel's house doesn't make it a fact.

Lucifer prowled around his brother’s second sex slave. He _wished_ that Castiel had sold the gorgeous little thing to him outright but being given full permission to personally train this particular slave into being a proper sex slave was a nice consolation prize. He hadn’t thought that Castiel would take him up on the offer but sometimes his little brother surprised him.

It was nice to know that Castiel wasn’t as possessive as Lucifer because if their roles were reversed he certainly wouldn’t have agreed to let someone else mold his slave.

He cocked his head to the side as he regarded Dean. Most sex slaves started very young in their training so that the lessons stuck and so they only knew of the one existence. This particular sex slave made it all the way to eighteen before he was claimed and had zero training unlike Daniel who had lived the opposite experience.

_Breaking him would make the lessons stick faster._

It was harder to train someone older but with the proper touch and teaching it was possible. He just needed to absolutely break Dean and then build the broken pieces into a sex slave he would be proud to sell from his sex slave house. Castiel hadn’t told him he _couldn’t_ use the hasher methods and Lucifer didn’t have the time to dedicate for a slower process.

Three days of sensory deprivation started the ball rolling and it was luck that Castiel’s basement, in the very back corner, had the perfect place for it.

He, of course, made Castiel’s servants clean the mess up three days later and made sure they didn’t remove the blindfold. Not a single one said a word as they cleaned the slave up, touching only when needed, as Dean sobbed and shook clearly trying to experience any kind of sensation available.

Afterwards the slave was led to a different room, the other really needed cleaning, before the servants left and Lucifer removed the blindfold. “Shhhhh.” He soothed as glassy green eyes looked at him, “We don’t want to do that again, do we?” Dean jerkily shook his head. “I know. Are you going to be good? Show me how good you are?” more jerky moves but this time nodding. “Good, slave.”

He settled down on the chair as Dean swayed and trembled where he stood. The cockcage and sound had been placed back on, Dean’s ass lubed and plugged after his thorough bath, along with the collar Castiel had given him.

“Now I want you on your knees in front of me and sucking my cock or they’ll put you back in that room.”

Immediately Dean stumbled forward, slamming to his knees and fumbling hands worked quickly to free Lucifer. Warm, wet heat wrapped around him as Dean started greedily sucking his cock.

Lucifer sighed, leaning back, while knotting his fingers in Dean’s hair and guiding Dean’s pace as that mouth made for cocksucking worked him over. It wasn’t as refined as a sex slave trained for years and years to give pleasure with their body but it wasn’t bad and his orgasm was building steadily.

He let Dean suck him until Lucifer lost his patience and started moving Dean’s head so he was fucking down his throat. The slave gagged when Lucifer forced his face against him, cock completely buried in his mouth, before pulling him back and repeating.

Slowly the struggles ceased and Dean relaxed, allowing himself to be used, as Lucifer worked himself towards his first orgasm.

Castiel’s home didn’t offer the same set up or items his sex slave house did but Lucifer would make do with what he had on hand. If need be he would ask Castiel if he could remove Dean to his sex slave house and use the facilities there for some of the more involved training.

He had plenty of sex slave trainers who would love to get their hands on a slave like Dean and they were experts at breaking a slave who wasn’t settling into their role properly which was clearly the problem here. Daniel had been thoroughly trained and had always been a perfect sex slave. Then Dean had been claimed and to Lucifer it seemed clear that Dean’s lack of training or understanding of his role was what was causing the problems.

Once he broke and molded Dean everything else should fall into place.

* * *

Dean’s arms were raised above his head, mouth gagged and eyes covered with a blindfold as Lucifer stepped around him. There were already welts along his back, thighs and ass from his first punishment.

It wasn’t enough considering Dean had disobeyed _three times_.

Lucifer narrowed his eyes. He had underestimated the animosity between the two sex slaves. Dean had been doing well, though he was put through sensory deprivation four times, and Lucifer had thought it was enough to introduce the other sex slave in the house to Dean’s training considering he knew Daniel had been given permission to use Dean during the day.

On top of that Castiel wanted to watch them together, wanted to be able to use them at the same time, so they needed to have no problems between them and Dean needed to follow orders with Daniel involved. It was very obvious that Dean _hated_ the other sex slave and Lucifer wouldn’t have his training come into question. He had promised Castiel his training would solve all of the problems his little brother was having in his household and Lucifer’s reputation would not be sullied by a stubborn sex slave.

Lucifer had not been amused when Dean had clearly, in addition to everything else, started pretending Daniel was hurting him in an effort to discredit the other sex slave. Unfortunately for Dean Lucifer saw through that ruse. Daniel had been thoroughly trained and had proven himself obedient over the years Castiel had owned him.

He spun the cane idly before stepping behind Dean and caning the swaying sex slave. Dean’s moans and cries were muffled by his gag as the chains holding him in place clanked.

It was a bonus that Dean looked beautiful whipped and caned. The marks showing up on his lightly tanned skin, Lucifer missed the deeper tan Dean had sported prior to becoming a sex slave, were gorgeous and Lucifer made a mental note to let Castiel know that Dean’s body would take pain play very well.

Lucifer continued to administer the punishment, explaining in a calm tone what Dean had done wrong and what was expected of him, as Dean jerked and cried until he was hanging limp while he was caned.

“Now we’re going to try this again.”

He pulled the blindfold off and lowered the chains so Dean’s arms were still raised over his head but his knees were on the ground. It was a delightfully submissive position.

“Daniel.” He called as the other slave stood up, cock free and skin unblemished, to walk over to him. The pretty slave’s cock was hard and Lucifer could see the heated arousal in his brother’s first sex slave’s eyes. “Your reward for being good.” He indicated to Dean and Daniel didn’t waste a moment.

As Lucifer settled into his chair he watched Daniel move to kneel behind Dean, shoving Dean’s chained legs wider apart, before guiding himself into Dean’s lightly lubed hole. There wasn’t a question that after being punished Dean wasn’t near as slick and open as he had been before he’d disobeyed. It was another part of Dean’s punishment. If he had been obedient from the beginning he could have enjoyed himself and avoided punishment altogether.

Daniel moaned, loud and drawn out, as he pushed in and Dean’s body trembled in the chains holding him in place. He didn’t pull away and instead hung there limply in his chains, head hanging in clear contrition, as Daniel’s fingers dug into Dean’s hips and he started _greedily_ fucking Dean’s ass.

The slap of skin on skin combined with the clank of chains and the moans of Daniel’s enjoyment had Lucifer hardening. It was a beautiful sight. He actually liked the use of a hierarchy in Castiel’s house and using the slave considered to be at the top of that hierarchy to establish Dean’s place as well as teach the slave how to be a proper sex slave.

It should be effective.

Lucifer watched Daniel fucking Dean and let the other sex slave enjoy himself. “Good job, _Daniel_.” He made sure to emphasis, “You’re always so quick to follow instructions. Always so good for your master.”

Punishing one and rewarding the other should help Lucifer achieve what Castiel wanted. His brother didn’t need to know the darker, finer details of breaking and training someone to be a sex slave especially one who had grown up outside of the slave class.

* * *

“Do _not_ stop riding that toy until I give you permission. I don’t care how tired you are, how much your muscles ache and protest…if you stop before I give you permission you’ll spend four days in sensory deprivation and an hour being caned.”

Dean’s cheeks were red from exertion, his body covered in a fine layer of sweat and his hitching, broken whimpers let Lucifer know how much it was costing Dean to keep moving.

In the center of the room, on the hard floor, Lucifer had affixed a large, thick dildo that he’d guided Dean down on over an hour ago.

It was important that Dean think of his master’s wants and wishes over his own limitations. That was integral towards being a good, obedient sex slave. Lucifer also wanted to build up the strength in Dean’s thighs and this particular exercise was good for the rest of Dean’s body as well. Dean should be able to be used for _hours_ if Castiel wanted it and he should be actively participating for every single second of it.

Lucifer wanted Castiel to have the option of offering Dean up for entertainment. All sex slaves were trained for that possibility and Castiel had more than enough gatherings that there were plenty of opportunities for his little brother to make those gatherings more _enjoyable_.

He could see where the toy pushed against Dean’s flat stomach, he’d chosen something extra-long and thick to impale Dean on, as Dean moved with desperation and exhaustion. Dean hated the sensory deprivation room and it had turned into a great punishment. It seemed more effective than actually beating the lesson into him.

Some sex slaves responded better to certain punishments but the sensory deprivation was the most effective and the quickest way to break a slave for proper training. Even the most stubborn and willful sex slave crumbled. At least that’s what he’d learned.

Lucifer watched the flex of Dean’s muscles and the way desperate green eyes _begged_ him for a break but Lucifer _knew_ his brother’s sex slave could go longer. It was especially important when Castiel paused to look into the room and Lucifer wasn’t about to let Dean have a break now.

“ _Faster_.” He snapped out and Dean jerked, eyes wide, but he moved _faster_ and with a kind of animal-like desperation that had Lucifer hardening uncomfortably in his pants. “I will tell you what you need. You do _not_ need to think. That is not your purpose. You are a _toy_. You are meant purely for others’ enjoyment and pleasure. Not your own. You don’t _get_ pleasure. You don’t _get_ to make choices. You are what your master says you are and you’ll do what your master says you’ll do.”

When Lucifer finally let Dean stop the sex slave was trembling, his chest heaving and Lucifer was sure the only reason Dean was still upright was the giant dildo holding him there.

That didn’t stop him. “Stand up.” Dean’s legs shook as he stood, “Kneel.” He lowered himself back onto the toy and Lucifer stroked his hair. “Good, slave.” Lucifer removed Dean’s gag, “Open.”

Dean’s mouth opened and Lucifer guided himself inside.

Green eyes slid closed, Dean’s muscles going pliant, as Lucifer helped himself to his own release. He roughly fucked Dean’s throat, shoving deep, while knotting his fingers in Dean’s hair and taking his pleasure.

There was no resistance, no fighting and Dean kept his throat relaxed as Lucifer used him.

“Good.” He offered again. “You’re being a good sex slave.”

* * *

It took months before Lucifer was confident that the lessons and punishments were successfully sticking. Mistakes and refusals, usually involving Daniel, were few and far between now.

Dean was turning into a well-trained sex slave. He was quick to hit his knees, to bend over and to follow any command Lucifer gave him. Castiel had taken to singing Dean’s praises whenever he used his sex slave or wanted to watch his slaves fuck while he relaxed.

He still planned on taking Dean to his sex slave house during the weekends for the next two months, Castiel had agreed after seeing how effective Lucifer’s training was, and Lucifer wouldn’t be confident until Dean had received at least a year of sex slave training but it was promising.

Once Dean had broken, and it had taken so much, he was a beautiful sex slave waiting to have behaviors reinforced, modified and added to make him perfect.

Lucifer wouldn’t consider it a success until Dean’s moves were completely fluid, there wasn’t a second of hesitation and when he saw Dean eagerly accept even the most taboo of orders from him. Those would mostly occur on-site in Lucifer’s sex slave house. It was important that Dean pass every single obstacle before Lucifer was finished.

Castiel was pleased, though, and Lucifer loved listening to his brother singing his praises to any and all who would listen. There was the added benefit of an increased interest in _his_ sex slave house and the sex slaves that his business thoroughly trained to go up for auction.

**Notes for the Chapter:**

> Hopefully none of you were shocked that Lucifer was clearly tricking Dean the first time he met him. Lucifer is a sadistic asshole who delights in the training of sex slaves and has a heavy hand.
> 
> Poor Dean.


	7. Chapter 7

**Notes for the Chapter:**

> This is a look at the impact of Lucifer's training from Castiel's eyes. Keep in mind that Lucifer isn't disclosing his training and that neither Castiel or Lucifer actually know the true dynamics between Dean/Daniel. Their views are biased.

Castiel had been allowing Daniel to seek release inside of Dean while he was away at work for six months now and he had noticed how Daniel’s disposition had returned to how it had been prior to him claiming Dean as a second sex slave. It had been an absolute relief to see his beautiful, eager sex slave behaving in the way that Castiel had enjoyed since he had first purchased Daniel.

It was also obvious that it had helped that he had also agreed to Lucifer’s second request when he had turned down selling Dean to him. His brother had offered to help train Dean into being a proper sex slave seeing as the boy had never received any training and Lucifer himself owned a sex slave house. Considering everything Lucifer had done for him over the years, and the fact that Dean had zero training, it had been impossible to pass up the offer.

There had been a noticeable change in Dean and that changed had brought nothing but harmony within his household.

Castiel had noted that the tension and the obvious aggression had steadily disappeared from his second sex slave. Slowly but surely it appeared as though Daniel’s use of Dean during the day coupled with Lucifer’s rigorous training had fixed the dynamics within the house after multiple hiccups in the first month. The green eyed sex slave was more docile, submissive and Castiel could see how Dean wasn’t overthinking each move when Castiel wanted to use him.

Slowly but surely Dean was responding like Daniel, sometimes even better, and Castiel loved that Dean seemed to take to sex slave training beautifully as he was molded into a sex slave that fit in Castiel’s household.

He enjoyed how Dean’s obedience had increased, how his movements were more fluid and whenever Castiel wanted to watch his slaves together Dean took Daniel’s cock without complaint just as he had always taken Castiel’s. His younger sex slave was now flourishing and the thorough use showed in Dean’s skills at pleasuring Castiel. He wasn’t sure of the experience Dean had brought with him when Castiel had claimed him, Dean had barely been eighteen, but now his skills were on par with those expected of an experienced sex slave.

Lucifer clearly knew how to handle and train a sex slave in the most effective manner. The weekends Dean spent at Lucifer’s sex slave house, receiving additional training that Lucifer explained Castiel’s home wasn’t equipped for, had an increasing obvious and profound effect each Monday that Dean was returned to Castiel’s home.

Slowly Castiel leaned back in his chair. He had just finished fucking Daniel while Dean watched, gagged and bound, and now he wanted to enjoy a good show. It took a little bit for him to get back in the mood but that didn’t mean he was in any hurry to leave his bedroom.

“I want you to ride Daniel, Dean.”

Dean managed to get onto the bed, arms bound behind his back, but Daniel had to help Dean with everything else. Daniel removed Dean’s plug and guided Dean so he was straddling his lap.

Strong legs, strength gained from riding Castiel and Lucifer when he was training Dean where Castiel had observed Lucifer forcing Dean to ride a long dildo until the slave had collapsed from exhaustion multiple times, Dean shifted and let Daniel guide him down onto his cock. Castiel groaned at the sight of Daniel’s cock, far too impressive for a sex slave meant to purely bottom, spread Dean wide and disappear into Dean’s tight hole.

Dean’s muffled groan filled the room, his pretty freckled cheeks flushed, as he took every inch of Daniel into his ass and soon he was astride Castiel’s favorite slave.

They really made a pretty picture and Castiel loved watching them move together. It was a good warm up before sex and a good show for him to enjoy between his own orgasms. This was certainly a bonus of having two sex slaves and he didn’t have to go over to his brother’s if he wanted a good show.

Daniel’s hands landed on Dean’s hips, fingers digging in to the freckled flesh there, as he urged Dean to move.

It was a testament to Dean’s increased strength as he worked thick thighs, bouncing on Daniel’s lap and greedily fucking himself on the other sex slave’s cock, as Castiel watched with arousal burning lowly in his gut.

They were sinful.

Castiel wished it was possible to fuck both of them at the same time but he was one man and he could only truly fuck one slave at a time.

It would change a bit when he finally married, his engagement was only in its fourth month, but he could enjoy spending a good portion of his nights getting lost in pleasure. And the marriage was an arranged thing, something he needed for heirs, so he would only need a little reorganization when his wife moved in.

“Faster, Dean.”

The mattress groaned lowly as Dean’s body moved faster and faster, vigorously fucking himself on Daniel, as Daniel moaned and fucked up into him with the same kind of eagerness that Castiel had noticed the first time he had allowed Daniel to fuck another sex slave.

He wasn’t surprised.

Castiel couldn’t imagine going for so long without getting his cock wet in a tight hole. It must be maddening and Daniel’s obviously improved disposition seemed to support it.

Fingers dug more into Dean’s hips, Castiel could see the way Dean’s soft flesh gave to Daniel’s grip over countless bruises already marking Dean’s skin, as the other slave started to urge Dean faster as he fucked up against Dean with increasing desperation that signaled his building orgasm.

Poor Dean’s cheeks were flushed, his eyes hooded and his chest heaved as he worked his body as best he could. Castiel could only imagine the painful need to come that Dean had to be feeling, cock caged and full of a sound, but completely denied.

Lucifer had explained complete orgasm denial with Dean was the best kind of training and Castiel had taken his brother’s suggestion to heart. After all that was how Daniel had been trained and how all of the other sex slaves were trained. Lucifer had said that he milked Dean once a month to keep the boy healthy and so Castiel wouldn’t have to worry about it as he reinforced the training Lucifer had already finished.

Dean’s turn around backed up Lucifer’s suggestion and proved that the changes in his treatment put him on the right path that would enable Castiel to keep both sex slaves without further problems.

Castiel could feel his own arousal building as he watched them moving and then Daniel was grinding Dean down onto his cock as he clearly came in the younger sex slave’s ass. He pressed against his hardening cock, groaning lowly, as Dean shuddered on top of Daniel and whimpered with need.

“Get him ready for me, Daniel.” He breathed out in anticipation. Dean ended up on his side, ass leaking come, as Daniel moved and started positioning Dean for Castiel. Dean’s face was pressed against the sheets, his back bowed and his knees spread with his sloppy ass offered up.

Come dribbled down from Dean’s fucked open hole and Castiel groaned at the sight. It really was an indulgence to have two of them and to have Daniel prepare Dean for him was an absolutely filthy extravagance he loved to enjoy.

Castiel hoped the delight he felt in this moment would translate to the event next week. At Lucifer’s suggestion he had decided to host a large gathering and offer Dean up as entertainment for all of his guests to use. It was supposed to be another test to see how Dean’s training held up and Castiel was hoping it would be a success. He’d been to a few gatherings with sex slaves offered and had, himself, enjoyed fucking the sex slave his host owned.

It had the added benefit of showing off his wealth and success to his acquaintances.

“My two pretty little sex slaves.” He breathed out, voice rough with arousal, as he climbed onto the bed and settled himself behind Dean. Castiel’s knees pressed to the insides of Dean’s and he spread them even wider as Dean whimpered into his gag but didn’t move. “Both of you always so obedient and eager to pleasure your Master.”

It was better that he’d turned down Lucifer’s offer to purchase Dean outright and instead had cut a deal to have Lucifer properly train Dean to better help his second sex slave fit into the house. After speaking with Lucifer it had been obvious that Dean’s lack of training was one of the main points of contention between his slaves. The other had been Daniel’s sense of security in his position coming into question and letting Daniel have a clear position within his household over Dean had fixed that.

Houses were supposed to have an obvious hierarchy and he had failed to establish that when he had claimed Dean. Fortunately that had been fixed and the house was once again running smoothly.

Everything had fallen into place after months and months of work. It was worth it.  

The first month Castiel had worried, Dean had almost always bore marks from Lucifer’s punishments and he was always bruised darkly, but something had broken in the second month and the marks had faded as Lucifer had reported a marked improvement in Dean’s training.

It was a bit unfortunate that the spark that had always been present in Dean’s eyes when he’d been a maid and then those first months as Castiel’s sex slave was gone, dulled or hidden, as Dean completed each level of training.

Some sacrifices had to be made and an obedient, eager sex slave who fit in perfectly in his house was worth the loss of that spark and fire. Dean wasn’t his maid, he wasn’t simply in the lower class, he was a sex slave and Castiel’s _property_. Castiel expected absolute obedience and eagerness from his sex slaves. The cost of Dean’s fire was only a small loss.

With anticipation thrumming inside of him Castiel guided the fat head of his cock to Dean’s loose hole and pushed in with a low, pleased moan of enjoyment as his sex slave shuddered underneath him.

There was _nothing_ like being able to constantly indulge in glorious, satisfying sex.

**Author's Note:**

> This story makes it 400 works posted to this AO3 account. I can't believe I reached 400. That just seems insane. I figured of all the fics I have in my folder this one, being so long, would be the best choice for the 400th spot. It basically has some of everything in it and a few things I had never done before.
> 
> Hopefully at least a few of you enjoyed this long string of connected prompts. I'm looking forward to reading any comments you might send my way!!
> 
>  
> 
> \--Yes I'm using this next bit on each of the new fics I post from my folder since it fits all of them (yay copy and paste).--
> 
> Again I'm still going through that folder on my laptop though I keep getting a bit distracted so this is getting dragged out a bit. This fic is another one that was waiting to be finished, fixed and posted.
> 
> Leave a comment and let me know what you thought. Your comments and thoughts are always appreciated! BOOM 400 FICS!! *screams and bursts into flames*


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